“My Best Icebreaker Is…”

Singles reveal their top tricks to get a conversation started. From the direct approach to the “fly-by”—try them yourself and watch what happens!

By Kimberly Dawn Neumann

ou know that moment: You spot someone across a crowded room, bar, bus, or produce section. You’d love to meet—but what the heck can you say to a complete stranger that won’t come off as dorky or desperate? Easy; try one of these real-world icebreakers that singles swear by. Why? Because these lines earned them plenty of dates.

Flirt with “fly-bys”
“My best icebreaking technique is what I call the ‘fly-by.’ It’s where you make witty comments of a relevant nature as you walk by the person who interests you. For example, this one time I saw a guy in the grocery store who was really attractive. So, as I
“As I pass someone cute at the grocery, I’ll say, ‘Go ahead and get the Frosted Flakes.’”
passed him in the cereal aisle I said, ‘Buy the Frosted Flakes—sure it’s all sugar, but everyone needs to eat like a kid now and then.’ Later when I saw him again in a different aisle, I said, ‘We have to stop meeting like this!’ and finally when we were near each other in the checkout line, I said, ‘Care to chill out over coffee after all this decision-making?’ He accepted!”
—Elizabeth Flanagan, Chicago, IL

The direct approach
“I have approached people in grocery stores, on the street, at bars, pretty much anywhere, and the best conversation starter I’ve found is just to say what I’m thinking. I’ll say something like, ‘Hi. My name is Josh, and I just wanted to let you know I find you incredibly attractive.’ Everyone on this planet likes to be found attractive. And even if they don’t want to date you, most will graciously accept your compliment.”
—Josh Prince, New York, NY

Survey says?
“Sometimes I pretend I’m doing a survey for a research project. People just assume it’s for a school or work project. My best ‘survey’ is to ask guys to tell me what they think
“Sometimes I pretend I’m doing a survey. It allows you to go up to anyone and just start talking!”
the ratio in this particular bar is of those who are out to actually meet someone to date versus those who are just out to have a drink with friends. It allows you to go up to anyone and just start talking... men and women! And you don’t have to worry about coming across as hitting on them. It’s all in the name of research!”
—Amy Brewer, New York, NY

Game on
“My friends and I like to play the typical bar games while we’re out—pool, darts, foosball, etc.—and you can use these games as an excuse to talk to whatever cutie you’ve been eyeing. For example, I walk up to a person I find attractive and say something like, ‘Hey, my friends and I are playing doubles at the pool table, but my partner left. Do you mind helping me out in exchange for a beer?’ It takes a lot of pressure off meeting someone because you’re being active, which leads to a more natural conversation like, ‘I can’t believe you made that shot! Do you play a lot?’ versus sitting at a barstool trying to force witty banter. I actually met two guys with this little trick.”
—Shannon Hamilton, Arlington, VA

Lay on the flattery
“One of the best ways to meet men is to pay them a compliment. Not just ‘nice tie’ but something really flattering. For example, one time on the way to the ladies room at a restaurant where I was having dinner alone, I noticed a very well dressed man. On the way back I stopped at his table and said ‘you are simply the best dressed man I have seen in a very long time’ and then proceeded on to my table. Within about five minutes he came to my table and asked if he could join me for dessert. My answer was yes.”
—Gloria Starr, Charlotte, NC

Questions, questions
“If I’m going to try to chat someone up, I make sure that my opening line invites a conversation. So if I see a woman picking up some curry sauce at Trader Joe’s, I’ll say,
“I’ll just say, ‘Hi. I just wanted to let you know that I find you incredibly attractive.’”
“Excuse me, I’ve always seen that sauce and wondered about it. How can you use it? Is it very spicy?’ Or, if I’m at a CD store, I’ll ask a woman in the classical section something like, ‘Excuse me, I’m just getting into classical music. Can you recommend something?’ In my experience, these kinds of questions really get you and the other person talking about your shared interests—which is a great way to bond.”
—Henry Bloomberg, Boston, MA

A little humor and humility can’t hurt
“I like to use what I call the ‘no pick-up line’ pick-up line. I mosey over and say something innocent like, ‘Excuse me for interrupting. I can see you’re busy reading (studying, working, whatever). You caught my attention so I thought I would risk public humiliation by introducing myself.’ My theory is it doesn’t really matter much what you say. If she’s keen, she’ll pick up the ball and respond with her name.”
— Bob Shepherd, San Diego, CA

Kimberly Dawn Neumann is a New York City-based writer whose work has appeared in Marie Claire, Prevention, and other magazines.
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